Triptorelin

Triptorelin
Clinical data
Trade names	Decapeptyl, Gonapeptyl, Triptodur, others
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	X;
Drug class	GnRH analogue; GnRH agonist; Antigonadotropin
ATC code	L02AE04 (WHO) QH01CA97 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Excretion	Kidney
Identifiers
	IUPAC name 5-oxo-D-prolyl-L-histidyl-Ltryptophyl-L-seryl-Ltyrosyl-3-(1H-indol-2-yl)-L-alanylleucyl-L-arginyl-L-prolylglycinamide;
CAS Number	57773-63-4 ;
PubChem CID	25074470;
IUPHAR/BPS	1177;
DrugBank	DB06825 ;
ChemSpider	17290424 ;
UNII	9081Y98W2V;
KEGG	D06247 ;
ChEBI	CHEBI:63633 ;
ChEMBL	ChEMBL1201334 ;
ECHA InfoCard	100.165.044
Chemical and physical data
Formula	C64H82N18O13
Molar mass	1311.5 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)[C@@H](Cc2c[nH]c3c2cccc3)NC(=O)[C@H](Cc4ccc(cc4)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc5c[nH]c6c5cccc6)NC(=O)[C@H](Cc7cnc[nH]7)NC(=O)[C@@H]8CCC(=O)N8;
	InChI InChI=1S/C64H82N18O13/c1-34(2)23-46(56(88)75-45(13-7-21-69-64(66)67)63(95)82-22-8-14-52(82)62(94)72-31-53(65)85)76-58(90)48(25-36-28-70-42-11-5-3-9-40(36)42)78-57(89)47(24-35-15-17-39(84)18-16-35)77-61(93)51(32-83)81-59(91)49(26-37-29-71-43-12-6-4-10-41(37)43)79-60(92)50(27-38-30-68-33-73-38)80-55(87)44-19-20-54(86)74-44/h3-6,9-12,15-18,28-30,33-34,44-52,70-71,83-84H,7-8,13-14,19-27,31-32H2,1-2H3,(H2,65,85)(H,68,73)(H,72,94)(H,74,86)(H,75,88)(H,76,90)(H,77,93)(H,78,89)(H,79,92)(H,80,87)(H,81,91)(H4,66,67,69)/t44-,45-,46-,47-,48+,49-,50-,51-,52-/m0/s1 ; Key:VXKHXGOKWPXYNA-PGBVPBMZSA-N ;
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Triptorelin, sold under the brand names Decapeptyl and Gonapeptyl among others, is a medication that acts as an agonist analog of Gonadotropin-releasing hormone, thus reversibly repressing of luteinizing hormone (LH) and follicle-stimulating hormone (FSH)[1][2].

It is a decapeptide (pGlu-His-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH₂) and a gonadotropin-releasing hormone agonist (GnRH agonist) used as the acetate or pamoate salts.

Primary indications include endometriosis, for the reduction of fibroids, for prostatic cancer, and to treat male hypersexuality with severe sexual deviation[2]. The drug has also been used off label to delay puberty in patients with gender dysphoria[3].

It was patented in 1975 and approved for medical use in 1986.[4]

Medical uses

Triptorelin is used to treat prostate cancer (PCa) as part of androgen deprivation therapy (ADT). Another ADT injectable medicine commonly used to treat PCa includes Lupron which also targets the pituitary.[5]

Another common use in the United Kingdom is for hormone replacement therapy to suppress testosterone or estrogen levels in transgender people (in conjunction with estradiol valerate for trans women or testosterone for trans men). Spironolactone and cyproterone acetate are other drugs used by trans people to suppress sex hormones, but these drugs have a completely different mechanism of action.[6]

Triptorelin has been used as a chemical castration agent for reducing sexual urges in sex offenders.[7]

Drug Action

Triptorelin is a Gonadorelin analogue, also known as Leuteinzing hormone releasing analogue (GnRH analogue, LHRH analogue).[8] The drug binds to receptors in the pituitary gland and stimulates secretion of gonadotrophins (namely luteinzing hormone and Follicle-stimulating hormone). This causes an initial phase of LH and FSH stimulation, prior to down-regulation of the gonadotrophin-releasing hormone receptors, thereby reducing the release of gonadotrophins in the long term, which in turn leads to the inhibition of androgen and oestrogen production.[2]

Side-Effects

General side effects can include:[2]

Anaphylaxis
Arthralgia
Asthenia
Asthma
Breast tenderness (males and females)
Changes in Blood pressure
Changes in breast size
Depression
Ovarian cysts
Mood changes
Skin rashes
Hot flushes
Weight changes

Contra-indications and precautions

Triptorelin should not be used for more than 6 months for endometriosis[2], and should be used with care in patients with metabolic bone disease and osteoporosis due to the risk of osteopenia.[2]

Society and culture

Brand names

Triptorelin is marketed under the brand names Decapeptyl (Ipsen) and Diphereline and Gonapeptyl (Ferring Pharmaceuticals). In the United States, it is sold by Watson Pharmaceuticals as Trelstar and by Arbor Pharmaceuticals as Triptodur (an extended-release 6-month depot injection). In Iran, triptorelin is marketed under the brand name Variopeptyl.

References

"gonadorelin analogue | Encyclopedia.com". www.encyclopedia.com. Retrieved 2019-09-21.
Joint Forumlary Committee (2018). British National Formulary (BNF) 70. London: Pharmaceutical Press. p. 635. ISBN 978-0-85711-173-9.
Barnes, Hannah; Cohen, Deborah (2019-09-20). "Gender dysphoria in children: puberty blockers study draws further criticism". BMJ. 366: l5647. doi:10.1136/bmj.l5647. ISSN 0959-8138. PMID 31540909.
Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN 9783527607495.
"triptorelin (Intramuscular route)". drugs.com. Retrieved 11 November 2016.
Wylie, Kevan Richard; Fung, Robert; Boshier, Claudia; Rotchell, Margaret (2009). "Recommendations of endocrine treatment for patients with gender dysphoria". Sexual and Relationship Therapy. 24 (2): 175–187. doi:10.1080/14681990903023306.
Study: Drug effectively treats pedophilia, CNN, February 11, 1998.
"gonadorelin analogue | Encyclopedia.com". www.encyclopedia.com. Retrieved 2019-09-21.